


An Unpleasant Series of Events

by KatieWrites



Category: Chicago Med, Chicago PD (TV)
Genre: Angst and Hurt/Comfort, Emotional Hurt/Comfort, Gen, Guilt, Hurt Jay Halstead, Hurt Will Hallstead, Hurt/Comfort, Introspection, Jay Halstead Whump, Kidnapping, Survivor Guilt, Will's just trying to do the right thing, beatings, bros, good person Will Halstead, hurt will halstead, protector Jay Halstead, protector Will Halstead
Language: English
Status: In-Progress
Published: 2020-01-05
Updated: 2020-12-15
Packaged: 2021-02-27 03:21:56
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 4
Words: 8,609
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22110253
Author URL: https://archiveofourown.org/users/KatieWrites/pseuds/KatieWrites
Summary: In which Jay and Will Halstead have a very bad luck.CH. 1&2 - Jay's just trying to solve a case...the aftermath was obviously his fault. Jay Whump.CH. 3  - Will just wants to stop kids from dying. That's all. Will Whump.CH. 4 - Will always knew his big mouth would get him into a life threatening situation one day. Will Whump.
Relationships: Jay Halstead & Hank Voight, Jay Halstead & Will Halstead, Will Halstead & Hailey Upton
Comments: 17
Kudos: 117





	1. All My Fault

**Author's Note:**

> Just a little something that popped into my head.

The case Voight had Intelligence working was grueling. It had been a week and there were no new leads on the kidnappers and their captives. The team members had been hitting the streets and coming down on their CIs, but no one had an idea of what they were looking for. At the start of the week, three aldermen and their families had been taken hostage. This kidnapping happened before a major vote on housing in the lower South Side of Chicago. With the three aldermen gone, the vote couldn't be made. So far, none of the aldermen nor their families had shown up. Voight was, needless to say, upset. 

Jay looked towards the Serge's office. He was currently on the phone yelling at whomever was on the other line. Apparently he wasn't getting the answers he wanted. With a sigh, Jay stood up and went to the white board again. There had to be something they were missing. No one was ever this clean when taking _one_ family hostage. There was no way that they could be squeaky clean taking _three families hostage_. "Halstead," Voight shouted as he opened his office's door. 

"Yes, Serge," he asked.

"I need you to go back through all of your CIs. Someone has to be holding out on us. Most of yours are based around our three Aldermen. I want them hard pressed."

With a nod, Jay went to work. He messaged all of his CIs, writing down when he would meet with them and leaving it on his desk-just in case something were to happen.

* * *

"Okay, Reggie. You said you had something," Jay sighed. This was the seventh CI he had met with in the last three hours. He was ready to head back to the station and see if anyone else was able to find a lead. Sadly, he had three more CIs to talk with after Reggie. 

"Maybe I do. What's in it for me, Bro?"

"How about no jail time and being able to see your kids grow up?"

"That's your deal every time, Man. This info deserves more."

"I'll be the judge of that, _Man_. You're already getting paid for your information. I have nothing else I can give you. Unless you want my boss to come down here and rake you over the coals for your information, I suggest you get on with it."

Reggie looked around, stuffing his hands in his pants. "Fine, Man. I heard on the streets that the Hustlers were planning on doing some big shit to stop the developments in the South Side. They think that the developments would hurt their business. Hustlers don't like new shits comin' in. Heard Red had somethin' big planned for the voters."

Jay studied Reggie, frown deepening as he looked at him. "What else? You're leaving something out."

"Man, this shit can get me killed. How do I know you're gonna protect me from them?"

"How long have we been working together, Reg?"

"Four years."

"How many times have you gotten burned?"

"None."

"So why do you think this time will be any different? What are you leaving out?"

Reggie sucked his teeth, but sighed. "Fine, Man. Word on the street is that Red's got some packages being held for the foreseeable future. Plans on making a point."

"Where are these packages being held?"

"I don't know man. I hear shit, tell you, and don't go askin questions that'll get me killed."

"Well, I need you to start asking about where Red is holding these people."

Reggie shook his head. "Absolutely not, Man. I'm not gettin myself killed just for your information. I got too much to lose, Man."

Jay's mouth straightened into a line. He hated himself for what he was suggesting, but it had been a week. He needed to make sure that the Aldermen and their families stayed alive. "Reggie, if you don't go around and ask about Red and his packages, I'm going to write up the file on your felony and you'll be shipped off for the rest of your life. Three strikes and you're out, Man."

Reggie's face hardened as he glared at the detective. He sucked his teeth, nodding his head, "so that's how it's gonna be, Halstead? Fine, but after this, we cool. You ain't got shit on me after this." 

Jay frowned but nodded. "After this, you don't owe me anything, Reggie. I'll tear up the case file and burn it."

* * *

Jay bounded into the bullpen, heading towards the whiteboard. At seeing the pep in Halstead's step, the rest of the team tuned into him. "Robert 'Red' Fuller. Head of the Chicago Hustlers. 37. Long list of priors including kidnapping and assault. Reggie said that word's been getting around that Red had some big plans in motion to stop the vote on the developments. He finally admitted that there was word that he had a few _packages_ being held for the foreseeable future and that Red plans on making some sort of point. I have Reggie reaching out in the community to see if he can get us more info on Red's plans."

"The second Reggie contacts you, I want you to get the information out of him. Burgess, Upton, Ruzek, Atwater: I want you to hit up the known associates of the Hustlers. I don't care if it's their wives, I want you to put the ear of God in them until someone gives us more information. Antonio, hit up your CIs and see if they can give us anymore information. Halstead, do a deep dive on all of the places Red owns along with known hideouts for the Hustlers. Talk to the Gang Unit if need be. Move people, we've already wasted enough time trying to find the Aldermen and their families." 

* * *

Jay slowly exited the vehicle and stood against it. Reggie was supposed to meet him to give him more information about Red and the Aldermen. He was honestly thinking that Reggie would never get back to him. He was half expecting Reggie to just sit at home with his wife and kids instead of look for information...but Jay was pleasantly surprised. If it all worked out, Jay would happily forget about Reggie's felony so that the man could go back to living his life. 

Jay looked down at his watch and frowned. Reggie was supposed to meet him ten minutes ago. An unsettling feeling wormed its way into his stomach. Reggie had never been late before. He moved to get back in his vehicle when three men emerged from the shadows. Two were pointing guns at Jay while the other was holding one to Reggie's head. "I wouldn't move if I was you, _Detective_. Wouldn't want to get the _Snitch's_ _head blown off_ would you?"

"What's your plan? My team will be looking for me before you even get me halfway across the city," Jay's voice came out smoothly as he put his hands up.

The leader of the group motioned for one of the men to take Jay's gun away. Jay let it happen, knowing that not only was he putting his life at risk, but his CI's. Some people think that CIs are like the dirt under a person's shoes. Jay doesn't believe in that. CIs are friends who help you out with cases. They become someone you know like you would know a friend. You come to know their family like you would your own family. Jay had already put Reggie in enough danger, the least he could do was make sure that Reggie stays alive so that he can go back to his family. 

After zip tying his hands, the three gangbangers pushed Reggie and Halstead into another vehicle. Jay could only hope that his team would catch on soon enough that he was missing...he also hoped that the three idiots kidnapping them would be dumb enough to forget to check him for his phone when they made another stop. 

* * *

"C'mon Man, Reggie didn't do anything. He gives me his wife's recipes so that I can impress the ladies. In return, I give him a slide on his illegal activities," Jay called out as he watched Reggie get beaten to shit. He'd been fighting with his bonds ever since they arrived at the abandoned building. He knew that they probably planned on killing both Reggie and himself...but he just had to keep both himself and Reggie alive long enough for his team to find them. "Seriously, we can hook you up with killer recipes." 

To be fair, Jay's brain was working at half speed. Whatever they had drugged him with was making it extremely hard to think. He was doing his best to come up with a believable lie...and he could make this believable...if only they would pay him attention. With another scream torn from Reggie's throat, Jay shouted at the men torturing him. "Back off. He doesn't know anything and there isn't anything you can get from him that you can't get from me! I know more about your gang and your operations than he does. Let him go, Man."

Red turned to him, a sneer on his face. Jay knew that he was pissed. He also knew that Red was going to do his best to make the torture last as long as possible. What Jay was hoping for was that Red would focus more on him than Reggie. "Reggie seems to not know a lot of things, Pig. What's the use of having him around?" 

Red raised a gun and pointed it at Reggie, "WAIT-" Red looked back to him. "You think you'll get me to tell you anything about Intelligence's plans if you kill him? That will shut me up quicker than you cutting out my tongue."

"Then you better start talking fast, _Man_ , or Reggie is going to be headless." 

"Let Reggie go and I'll tell you everything I know."

"That's not how this works _Detective,"_ he spat, gun firing. 

Jay had seen enough casualties in the war. He'd heard countless rounds fill the air. He'd seen his fair share of wounded and dead men and women while he was serving. He'd seen countless dead bodies through Intelligence. He'd heard pistols fired more times than he can count...but he hadn't heard the sound of the bullet hitting flesh in the longest time. It wasn't something he wanted to remember. It wasn't something he'd wanted to witness. There was no scream, no shout, no pleading from the one who was shot. There was only a dull thump that resonated in Jay's head.

Reggie was dead.

Reggie was dead, and it was his fault. 

Reggie had a wife, kids...and they wouldn't have Reggie with them because of him.

If he hadn't have pushed Reggie to get more information, he would still be alive. It was Jay's fault that Reggie was dead, staring lifelessly at him from across the room. 

Jay's mind was blank. The only thing going through his head was _Reggie's dead. Reggie's dead._ He couldn't seem to focus on anything else. He didn't move, didn't say a word. He just stared at Reggie thinking that it was his fault. He couldn't even pay attention to his captors. Nothing else mattered in that moment.

It seemed like forever before there was someone crouching in front of him. Voight. When did he get there? He hadn't even heard the team's entrance. From looking around the room, it seemed like he hadn't even heard the firefight. All Jay could do was think about Reggie...he couldn't even respond to Voight as he saw the man's mouth moving. Jay knew that he was most likely going into shock, but he couldn't really focus enough to be worried about it. "It's all my fault," he finally spoke as he looked to Voight. "I got Reggie killed." 

"No you didn't, Jay. That's not on you. C'mon, we're going to get you to Med and then we'll talk more."


	2. All My Fault Pt. 2

**Summary for the Chapter:**

> A continuation of the last chapter!  
> Jay just wants to make up for Reggie's death.

No matter how much he argued with Choi, he couldn't get out of being admitted to the hospital. When he had arrived, Will had been on him immediately. He didn't understand anything that Will had been saying to him. He had seen Conner pulling Will away so that Choi could work on him. He knew that there was nothing seriously wrong with him. The drugs that had been in him system were nearly through their course because Jay felt more alert than he had the whole time he'd been captured. Other than some bruising and a sprained wrist, he was sure he was physically fine...unlike Reggie. But here he was, in a hospital bed waiting to be discharged (which he knew wouldn't be happening any time soon if Will had anything to do with it).

Speaking of Will, since he'd been moved from the ED, Will had been with him every step of the way. Don't get Jay wrong, he's happy and grateful that Will wasn't letting him go through this alone...but he really didn't need Will's constant mother hen routine. It didn't help that Will kept trying to get him to tell Will what happened. He knew Will just wanted to help, but he just wanted to forget it ever happened. 

"Okay, so I saw Choi. Looks like he has some test results. I brought you some of the good jello from the cafeteria. And I was able to convince Ms. Goodwin to let us have the premium channel to watch the game." Jay looked up as Will placed the jello in front of him. He didn't deserve the treatment he was getting. Why did no one understand that he got a man killed...that he caused a family to lose someone they loved? He needed to go and apologize to Reggie's family. "Jay?" 

He cleared his throat, "Yeah, yeah. Heard you."

Before Will could respond, Dr. Choi entered the room. "Jay. Good news, the drugs in your system shouldn't have any lasting effects. The Tox showed that there were multiple drugs in your system. They all created a cocktail that caused you lose time and feel unsteady. It was a mix between a tranquilizer and a stimulant, probably so they could try to still get information out of you while making sure you were out of it enough to not cause any trouble. In a few hours, I'll discharge you as long as you stay with someone."

"I don't need a babysitter, Ethan."

"With my medical opinion, I think you do. Will probably isn't going to let you out of his sight for a few days anyway. Now, you can't go back to PD until you have a follow up with me about your sprain. I'd say you'd be able to return to work in a week and a half."

"C'mon," Jay groaned. 

"No arguments."

* * *

Will was getting on his last nerve. If he had to hear his brother ask him if he was feeling alright one more time, he was going to scream. He needed to go to Reggie's family. He was sure that they knew by now that Reggie was gone...but it should have been him that told them; it should have been him that didn't survive. He sat up in the bed that Will had put him on. He hadn't heard any sounds coming from the other room in a while. Hopefully Will was asleep and he could finally go talk to Reggie's family and tell them how sorry he is.

Quietly, he exited the bedroom and walked down the hall. The only light he could see was the glow of the television. He assumed Will had dozed off on the couch. Just as he passed the couch he heard a sigh, "What are you doing Jay? You should be resting."

Jay froze, silently cursing himself. "I have some things I need to take care of at the station, Will."

"Ethan told you that you don't get to work until you have another check up with him and he clears you for work. Go back to bed." Will had made his way over to Jay. In the dim light, Jay could see the determination in Will's face. He assumed Will could see the determination in his face as well, because he continued on. "I don't know what you went through when you were captured, but I know nothing good happened. If you want to talk, I'm here. Whatever you need, I'll try to make sure you have it."

Jay scoffed. If only Will knew. "What I need is to go talk to my CI's family."

"We can go tomorrow. It's 3 in the morning, Jay. First thing after you get some sleep, I'll take you wherever you want to go."

Jay knew he wasn't going to get anywhere with Will. He also knew that he wouldn't be getting much sleep even with how tired he was feeling. The only thing he could see when he closed his eyes was Reggie being shot. He could hear everything around him in the moment. He could hear the gunshot, hear it pierce through Reggie's body, see Reggie plop to the floor. He knew he wouldn't rest.

"How about we watch last week's game? You were working so much I know that you never got to see the whole thing."

* * *

True to his promise, Will drove him to Reggie's place the next morning. Jay didn't move as the car parked. He had no idea what to say, he just knew that he needed to tell them how sorry he was. As he unbuckled his seat belt, he heard Will's door shut. He knew Will wasn't going to let him do this alone...and he was kind of thankful for that. 

Slowly, Jay exited the vehicle, stuffing his hands into the pockets of his jeans. Will clapped his shoulder in silent support as they approached the door. As much as Jay wanted to turn back, he knew he couldn't. All that filled his mind was Reggie and how he would probably be alive if he hadn't pressed...if he hadn't asked Reggie to dig more. If he had just left Reggie alone, he'd get to watch his son and daughter grow up, he could have taught his son to be a better man and not get in trouble. He could have scared off all the men related to gangs so that his daughter would grow up to be anything she wanted to be. Reggie had people to come home to, Jay didn't.

He didn't even realize that his hand had reached up to knock until he was lowering. He didn't have to wait long before Aelishia answered. She wiped at her eyes as she opened the door and immediately the air felt colder. The glare that was leveled at him spoke of how much pain she was in and it was all his fault. "What the hell are you doing here? Haven't you done enough?"

Jay licked his lips. He had no response. He honestly didn't know what he had planned to do here other than try and apologize but that seemed trivial at this point. "I-I'm so sorry," he finally got out, hearing his voice crack.

Aelishia scoffed, rolling her eyes as they welled up with more tears. "Fuck off. You've done enough damage, _Detective_. Reggie wanted to turn his life around. He wanted to make up for all the wrong he did because he believed his children deserved to have a good father and he was convinced that he wasn't a good father because of what he did as a teen and young man. He was better and he helped you on so many cases and in turn you got him killed! If he hadn't been asking about the Hustlers-" she sobbed, unable to keep talking.

"I-I know. There's no excuse I can give you to make this up to you. I-I pushed too hard..." Jay trailed off, he wasn't sure what else he could say. He knew he wouldn't be able to console her, but he had hoped he'd be able to ease the pain. He just wanted a way to keep her from hurting because of him.

"So you just came down here to apologize and tell me how guilty you feel? What were you expecting? Forgiveness?"

"No! No I wasn't expecting you to forgive me...I wanted to see if there was anything I could do to make this any easier for you. I know-If you need arrangements or-or anything...I just want to make this easier for you."

She glared at him. "You know, there is something you could do to make this easier for me. You can get the hell off my property and never show your face again." The door slammed in his face and Jay let out a shaky breath.

"Come on Jay, let's go."

**Notes for the Chapter:**

> So this is probably the last continuation of the previous chapter because I don't know where else to take it.


	3. Just Trying to Help

**Summary for the Chapter:**

> Will just wanted to do something nice for his brother. Jay had been stuck with a pretty gruesome case all week and Will just wanted to help. So what if he went through Jay's files and happened to know someone on the South Side that might be able to help? So what if he didn't tell Jay he was going to meet this person? It's not like Will thought that this would go sideways...he was just trying to help so he didn't have to see that vacant look in his brother's eyes...he never wanted to see that look in his brother's eyes again.

Will just wanted to do something nice for his brother. Jay had been stuck with a pretty gruesome case all week and Will just wanted to help. So what if he went through Jay's files and happened to know someone on the South Side that might be able to help? So what if he didn't tell Jay he was going to meet this person? It's not like Will thought that this would go sideways...he was just trying to help so he didn't have to see that vacant look in his brother's eyes...he never wanted to see that look in his brother's eyes again. 

For the past week, young men and women had been coming into Med and other hospitals overdosed or killed in some other way. The Intelligence team was running on fumes and Will was tired of pronouncing children and teens dead. If Will could help and stop the death of these young people, he wanted to. So, Will had waited for Jay to crash and went through his case files. Intelligence had looked into the Three Gs Gang, the Latin Kings, and others not associated with either gang. So far, they had nothing. According to Jay's case notes, the team were pretty sure the overdoses related to a loner, not involved with the gangs. According to the labs on the teens that Will had run the previous day, the Heroine had been cut with fentanyl. Honestly, the Heroine probably wouldn't have killed all of those kids had it not been cut with fentanyl to cut own the price for the drug runners. 

All this to say, Will found himself on the South Side because he knew a former member of the Three Gs and thought that, maybe, he could help. "Chang, my man," Will greeted, a smile on his face, "I'm cashing in on that favor you owe me."

"Will, what can I help you with?"

Sitting in front of Harry Chang, Will took the offered drink. "You hear about the overdoses skyrocketing in kids this past week?" At Chang's nod, he continued, "I know it's not your scene anymore, but do you have any idea who might be behind it? They're cutting Heroine with fentanyl, that's deadly, man. I can't keep watching these kids die, man." Will stared at the table for a minute before lifting his head to look at Harry. "Harry, if you know anything, tell me or let me give you my brother's contact information. Please, it's killing me inside with each kid that gets rolled through my ED."

Harry's lips formed a thin line. "Will, what you're asking-"

"I know what I'm asking. I promise that nothing will blow back on you. Just-you just have to give me a name that I can give to my brother. You won't even enter the conversation." 

Chang sighed, shaking his head. "Will, you shouldn't be here asking about this," he whispered. 

Will huffed, staring straight at Chang. "Harry, I asked nicely, now I'm telling you. If you know anything, tell me. Then you don't owe me anything."

Silence engulfed the pair. The empty bar seemed bigger as Will waited for Harry's answer. After a few minutes, Harry looked away from Will. "Let me call around."

* * *

Will, like a dumbass, didn't leave. He wanted the information as soon as possible so that he could tell Jay and he and Intelligence could get the shit drugs off the street. Really, with Harry's resistance upon the request when it was first introduced, Will should have realized something was up. Will could blame it on the fact that he hasn't slept in twenty-four hours...well, Jay wouldn't be looking for any of his excuses when he got his hands on him. Honestly, Will should be more worried about what would happen to him when Jay saves his ass...because he's pretty sure that Jay would kill him. 

About an hour after Chang 'called around', more people entered the bar, even though it wasn't time for the bar to open. Will had felt his back tense as he got a look at the men. Definitely members of the Three Gs. Will mentally hit his head against the table he was seated at. He should have at least told Jay he was going to 'see a friend'. Reaching into his front pocket, Will dialed his first emergency contact, Jay. He just hoped Jay would be able to hear enough to help him out...and he really fucking hoped that Jay actually answered and stayed on the line when he got no response from Will. 

As the men approached him, Will forced a smile, "hey fellas. Why don't we just forget I was here, yeah?"

"Look, we got a comedian," the first male glared. 

"Look, I don't know anything. I don't even remember why I came down here. It certainly doesn't involve impure Heroine or who it came from."

"We can't let you leave," another man stated. "You came into Three Gs territory, asking about us, and you think you can leave?"

Will wasn't prepared for the first punch the man threw, but he did scramble away from the next attack. "To be fair, I wasn't asking about the Three Gs. The South Side is a big place, okay? I was just wondering if Chang knew about _anyone, not just gang affiliated people,_ that could have been selling the Heroine that has killed so many youths. You know, I have to pronounce them dead, I hate seeing dead kids, man. Now, let's forget about this. I don't know anything. I just got lost on my way home." Will spoke faster as the men approached him. 

The first man chuckled, pointing to him. "White Boy thinks he can talk his way out of here. We're not going to let you just walk out of here and open your big mouth the second you get a chance to." He turned to his friends, "get him." 

"Wait, wait, wait. Let's talk about this." Will struggled with the men, trying to get them off of him. "Let's talk about this!"

"Shut him up," the first man growled.

* * *

Jay was already on his fourth pot of coffee and his last bit of sanity when his phone began to ring. He thought about ignoring it when he saw his brother's contact information pop up. Making his way back to his desk, he sighed. It was a little unusual that Will would call him when just got off shift at Med. Nodding, he picked up. "Will, this better be-"

_"Why don't we just forget I was here, yeah?"_

"Will? Did you butt dial me again?"

There was something said in the background of the call that he couldn't make out.

 _"Look, I don't know anything. I don't even remember why I came down here. It certainly doesn't involve impure Heroine or who it came from_."

Jay's head shot up, he put his phone on speaker. "Trace Will's phone now," he called out. 

_"We can't let you leave. You came into Three Gs territory, asking about us and you think you can leave,_ " a voice closer to the phone asked. Jay sucked in a breath, he was going to kill his brother when he found him. He could hear a scuffle on the phone. He looked up to see Voight joining the team.

 _"To be fair, I wasn't asking about the Three Gs. The South Side is a big place, okay? I was just wondering if Chang knew about **anyone, not just gang affiliated people** , that could have been selling the Heroine that has killed so many youths. You know, I have to pronounce them dead, I hate seeing dead kids, man. Now, let's forget about this. I don't know anything. I just got lost on my way home_," Jay could hear the panic in Will's voice, but that was probably only because he knew his brother so well. To a stranger, it would just sound like someone trying to make a point while trying not to get into an altercation. 

Jay cocked his jaw as he heard someone laugh at his brother. First, he would deal with these pricks, then his brother. _"White Boy thinks he can talk his way out of here. We're not going to let you just walk out of here and open your big mouth the second you get a chance to. Get him."_

 _"Wait, wait, wait. Let's talk about this."_ More rustling came across the phone. His brother was likely being dragged to an unpopulated place or a vehicle. _"Let's talk about this!"_

_"Shut him up!"_

There was more scuffling heard before a pained grunt came from the phone and he heard a thud. He couldn't tell if it was his brother for a second. _"Little bastard, knock him out if you have to."_

"I got him. He's at a bar in China Town. Sent the coordinates to your phones," Mouse called. That was all Jay needed to race down the stairs. 

* * *

"Jay, slow down. We don't know how many people are down there," Voight growled. 

"My brother's in there, that's all I need to know," Jay retorted, not slowing down at all. 

Antonio stepped in front of Jay, keeping him from walking further towards the building. "Mouse is going to give us a number of cell phones in the place and then we'll come up with a plan. Then, we'll get your brother out of there."

Their ear pieces crackled to life, _"Unless there are people without phones in there, I have five phones. One of them is Will's. So, there should only be four assailants."_

"Alright, we outnumber them. Two people cover the back, the rest of us go in hot. Simple," Jay cocked an eyebrow at Voight. 

Voight nodded slightly. "Alright, let's go with that plan. Al and Burgess, cover the back."

Upon entering the bar, there was one man behind the bar. Harry Chang, the owner of the bar. According to his record, he was a former member of the Three Gs. Seems like that might not be the case much longer. Kevin and Ruzek took care of him. Antonio, Hailey, Voight, and Jay continued to clear the bar. Softly, Antonio caught the others' attention. "Got a basement."

They converged on the basement, entering the stairwell silently. The sight that greeted them at the bottom had Jay's finger reaching for the trigger. "CPD, put the cables down," Antonio shouted. One of the men reached in his waist band, Hailey didn't hesitate to shoot the man. Voight and Antonio quickly took care of the other two men while Jay went to his brother. "Will, hey, Will?" Putting his hands on his brother's face, he barely hid the hurt expression when Will tried to jerk away from him. "Hey, it's me. It's Jay. I've got you."

Blood was running down a cut in Will's hairline, making it hard to see much more damage on his face. Jay could tell that Will's right eye would swell shut soon enough. The red burn marks across his brother's chest made Jay want to ask Voight for five minutes alone with the pricks who did this to his brother. But, Jay had priorities. The shallow cuts on Will's chest seemed to be clotting. Grasping his radio, Jay called for an ambulance. 

Getting will up the steps was a challenge in and of itself. Will refused to be carried up, he almost refused the helpful shoulder he was leaning on, but Jay wouldn't let that happen. It was a slow trek, but the brothers made it. Will limped across the floor of the bar, stopping as he saw Kevin and Adam starting to lead their offender out the door. "Wait," he called. 

Adam paused, causing Kevin to do the same. Will, unsteadily, made his way towards the man in cuffs. "I asked you to help me because kids were dying. I asked you to help me because I thought that, somehow, after watching your sister be gunned down you had a change of heart. You called me, crying, because your sister was dying. I showed up at your house at three in the morning after having worked thirty hours straight to help your sister because you were afraid that she'd get taken away from you if you went to the hospital. I asked you to repay that debt to me and you fucking set me up!" By this time, he had reached the man. "I didn't say a word to my brother. I saved her. All I asked for was information. I wasn't even going to bring your name up when I gave the information to my brother, man! What, did you get back in the gang? After what they did to your sister? Fuck you," Will growled. Before anyone could react, Will sent a punishing punch into Chang's face. The crunch of the cartilage in Chang's nose was the only sound in the room. "Your sister deserves so much better," Will seethed.

Jay pulled Will back, "get him out of here," he stated. "Calm down," he turned to Will. "You're in no shape to try and fight me off Bro."

"I just wanted to help. I just wanted to stop more kids from dying...I thought he was out," Will muttered as Jay helped him into a chair. 

Jay sighed, "I know. Next time, though I hope there won't be a next time, bring me with you."

Will laughed lightly. "I think I'll leave the detectiving up to you, Bro."


	4. Healer, Fixer, Protector?

**Summary for the Chapter:**

> Hell, he should have just given Hailey the childhood story she was looking for...then, maybe, they wouldn't have still been in the diner when this shit hit the fan. Maybe he would be on his way to his shift and Hailey would be out on whatever the latest case for Intelligence was. Then again, maybe if they hadn't been here, no one would have seen the man and figured he was up to no good. Maybe someone would have died by now. So far, no one was hurt. The gun was pointed at Will, it was totally possible that the man would have shot the cashier the second he reached the register. Maybe there was a reason he was still here when the man walked in. He was a healer, a fixer, he lived to protect and help those in need. So far he was protecting and helping those in the restaurant who didn't currently have a gun trained on them because it was trained on him. 

"Come on, you can't be serious," Will raised a brow at his brother's partner. "Hailey, I'm not going to help you win a bet against my brother. I value my life and the free drinks I get from his fridge on Saturday nights."

"Will, think about it. Two hundred dollars and I'll split it evenly with you," she exclaimed as she stirred the straw in her coffee around the cup. 

Will chuckled. "No, I happen to be fine in the financial department. Seriously Hailey, why does this matter so much to you? Other than the fact you stand to win or lose two hundred bucks." Will relaxed back into the booth as he waited for Hailey's response. 

"Okay, I want to know more about my partner, alright? He bet two hundred dollars on the fact that I wouldn't be able to find out any of his childhood antics. I have until the end of the week to actually come up with one, but I need details. Will, please...I know there's at least one story that won't put you in the dog house but that will get me two hundred dollars!"

Will shook his head. "I'm sworn to secrecy."

Hailey groaned. She knew it was a long shot to try and get Will to divulge anything on his brother...but she had to try. Will tried to pay attention to Hailey as she continued to try and get him to spill childhood secrets, but his attention was drawn to the man entering the small diner. A ball cap was pulled firmly over his eyes. His coat was extreme for the mild temperatures Chicago was experiencing. Something felt off about the guy. Will gave a small mumble to Hailey as she continued to try and get a story out of him...he should probably tell her that he feels uneasy about the man walking their way. They were seated near the cash register...was this man going to try and rob the store?

Will licked his lips, eyes moving away from the man as to not draw his attention. "Hailey, I think you should call a unit," Will stated before standing up and 'accidentally' bumping into the strange man, Will's drink spilling all over the man's front. "Oh, Man...I'm so sorry. I didn't see you there. Let me buy you breakfast or something." Will turned on his charming grin as the man turned to glare at him. "Look, no hard feelings. C'mon, I'll buy your breakfast."

The man's hand reached into his jacket and Will felt his heartrate begin to climb. Will held his hands up as the man leveled a gun at his chest. "Whoa, all this over a spilled drink? I said I was sorry, Man!" Will could barely make out Hailey whispering into her radio as the screams of the patrons filled the air. 

Three shots filled the air as the man raised his pistol and fired into the ceiling. "Everyone down on the ground," he shouted, gun going back to Will's chest. "You, go lock the door." The man followed him as he walked towards the door and pushed the lock into place. As the first patrol car pulled up, the man got behind Will, placing the gun to his head. "Draw the blinds." Will did as he was told. By the time the last of the blinds were drawn, Will could see the Intelligence team standing with the patrolmen, trying to figure a way in to help those in harms way. Will can't help but think maybe he should have said something sooner. Maybe then there wouldn't even be a hostage situation in the first place. 

Hell, he should have just given Hailey the childhood story she was looking for...then, maybe, they wouldn't have still been in the diner when this shit hit the fan. Maybe he would be on his way to his shift and Hailey would be out on whatever the latest case for Intelligence was. Then again, maybe if they hadn't been here, no one would have seen the man and figured he was up to no good. Maybe someone would have died by now. So far, no one was hurt. The gun was pointed at Will, it was totally possible that the man would have shot the cashier the second he reached the register. Maybe there was a reason he was still here when the man walked in. He was a healer, a fixer, he lived to protect and help those in need. So far he was protecting and helping those in the restaurant who didn't currently have a gun trained on them because it was trained on him. 

Will mentally chuckled to himself. His sense of priorities would be called 'screwed' by his brother, if he knew that Will took some comfort in the gun being pointed towards him and not other people in the diner. Hell, Will would call his brother a hypocrite for the fact that he knew that his brother would feel the same comfort if he were in here with the gun pointed towards him. Maybe it was the big brother instinct that made him feel comforted, maybe that was why the protector instinct was stronger than his need to shrink away from the man with the gun. Hell, he'd been worried about Hailey getting hurt, that's why he hadn't said anything sooner. Jay would _kill him_ if he let his partner get hurt...well, Jay would probably kill him either way considering that the aforementioned statement could still happen and the fact that Will decided to solve this whole stranger danger feeling himself in the first place.

Okay, so maybe Will hadn't thought this far in advance. His first instinct had been to stop the man from making it to his destination, which could still be debated as to whether it was the right call or not. He hadn't really thought of where to go from there. He did have the fleeing hope that the spilled drink would have caused the man to leave the store and not brandish a weapon at all, if the man had a weapon in the beginning. Apparently, even a spilled drink wouldn't deter this man. The man shoved a bag in Will's hands. "Open the register and put the money in the bag."

Will was never really good at negotiating with people who pushed him around. Growing up in Canaryville, you didn't let people just walk over you. Hell, Will's always let his big mouth get in the way of making peace with different situations. He mouthed off to his dad when he decided to be an ass about his profession and Jay's. When he first met Connor Rhodes, he fought him with words, didn't let up because he wasn't going to let this _trauma surgeon_ tell him what to do. He got into it with Goodwin on many occasions...so it shouldn't be a surprise that even with a gun pressing into his back, he couldn't just do the task the man wanted silently. "I don't know if you noticed, Dude, but there's an entire police force outside this building. I don't think you're going to be able to just walk out with this bag of cash and _call it a day_."

" _Shut up_ ," the man growled.

Will chuckled out loud this time. "What? Don't like it when your hostages talk back to you? Man, all I did was spill a drink on you and then you go all broody caveman and pull a gun?" In his head, he could hear his brother telling him to keep his trap shut...but he's also never been good at following orders, so it doesn't phase him. "Look dude, best case scenario, you walk out of here in cuffs with not a scratch on you head. Worst case, you go out in a body bag. It's your choice really. So, does the cash really matter? Have you never seen a cop show about hostage taking? The big bad never gets to leave with the cash or whatever he was after in the first place."

The abrupt crack to his temple led Will to stumble as he was pushed to the register. A quiet groan left his mouth. He could feel the blood start trickling down his face. "Not cool, Dude. I'm just trying to help you out."

"You are the mouthiest cop I've ever met," the man rolled his eyes, gun not leaving Will's back again. 

Will made an affronted noise, eyebrow raising as he turned slightly to look at the man. A laugh left his lips, "you actually think _I'm_ a cop?" He laughed again. "Man, you wouldn't know a cop if they pistol whipped you in the face." Will never said he was the _best_ negotiator in the world. Hell, he was flying by the seam of his pants here. Hearing the click of the safety, Will quickly sobered up, laughing stopping. "Uh, that didn't come out right," he cleared his throat. 

"Cash. In the bag," the man roughly pushed him into the register. 

"Right. Cash. In the bag. Uh, I need a code to get in." A scream was torn from a female worker as she was pulled up by the hair to stand next to Will. "Hey! Easy Fido, I'm sure she would have gotten up had you asked nicely!" The gun turned towards him again as the man sneered at him. "Right, just uh...please put the code in so that I can get the money out for this _patient gentleman_ ," he gave a tight smile to the young woman. 

As soon as the code was in, the man pushed the young woman back onto the floor. Will made eye contact with Hailey as he stood in front of the money. She shook her head and he gazed back down at the cash filled drawer. Was that a _no don't do anything_ shake of the head or _no don't give him what he wants or he'll shoot you_ shake of the head? "Have you ever thought about entering the Hollywood scene? You'd make a good _Thug Number One_ in a movie or TV show." Or maybe the head shake was the _Don't antagonize the man with a loaded gun pointed at you_ head shake.

The gunshot made Will jump. The bullet lodged just inches from his left hand that rested on the bar next to the register. "I'm not going to tell you again! The next bullet will go through your head," the man screamed.

Will gulped, finding it hard to breathe around the lump in his throat. Will's hand shook slightly as he started to pile the money into the bag. Once the register was empty, Will held the bag out for the man. "We're not done," he growled. Picking the young female up from the floor, he continued, "your safe. I want the code."

"I-I-I don't know it," her voice shook. As the man raised the gun to her head, she cried out, "I don't know it, I'm not the manager." Tears were rolling down her face. 

Will found himself moving again. He got between her and the man, "she said she doesn't know. Leave her alone," he growled. Will didn't flinch as the gun made contact with the middle of his forehead. He glared at the man, "what? Going to shoot me now? Go ahead. The second you do, a round is going to go through your head. I suggest you kindly ask who the manager is and ask them, without the gun pointed at them, that they give you the code. You and me can, then, go into the manager's office and get the money from the safe. I bet the manager even knows a way you could get out of here without the police seeing you. Places like this always have a secret exit that isn't in the blueprints."

The man's face hardened. He and Will stared at each other, neither one moving. Slowly, the gun lowered so it was leveled at Will's chest again. "Fine. I want the manager to slowly stand up or I'm going to start shooting your workers."

Will let out a breath he didn't know he'd been holding as the feeling of the gun on his head dissipated. He honestly didn't know where the bravery-or was it stupidity-was coming from as it became more likely that the man was going to kill Will when he was finished with his plan. As the manager slowly made her way towards them, Will did his best to come up with a plan to get out of this alive. He knew the second that the safe was cleaned out, the man would most likely put a bullet in his head. Will glanced over to Hailey, seeing her creeping forward at a slow pace. She'd been doing that since this whole thing started. She didn't have her gun as her shift hadn't started yet. Will had made it clear that they could have breakfast as long as she 'didn't bring her gun to threaten him with' if she didn't get the answers he liked. It was more based on the fact that Will hated guns. He absolutely hated them and the one thing he asked whenever he met with any of his brother's friends is that their guns were out of sight. Clearly he'll have to revise his stance once he gets out of this alive.

Will's brought back to the present as he's yanked forward. Slowly, Will walks in the direction the man pushes him. As they enter a hallway, Will can feel the shaking spread to the rest of his body. "Let's be real here, okay? No matter how hard you try, you're not getting out of here as a free man. Hell, I'm pretty sure that you're going to shoot me in the head the second that safe is cleared of its contents. What's you're plan here?"

"I'll worry about that. Open the door."

Will's not quite sure what happens between this moment and the next. One second he's opening the door to the manager's office and the next, he hears two gunshots go off. It takes him a minute to feel the pain in his side as he looks in confusion at Antonio and his brother. He can make out their mouths moving, and, in the back of his head, he understands he's probably going into shock, but in this moment, he's just confused. How had Antonio and Jay gotten into the diner?

* * *

Sound was the first thing to come back to Will once he came back to awareness. He could hear the constant beeping of what he knew to be a monitor in the hospital. He bet he was at Med, it would have been the closest hospital to the diner he and Hailey had been at. Hailey...was she alright. Will forced his eyes open as he heard the beeping on the heart monitor speed up. He tried to push himself up. He needed to make sure Jay's partner was alright, that she hadn't been hurt. There had been two shots when he opened that door. He knew one hit the man behind him. What if the man had a partner? What if they hurt Hailey.

"Hey, hey, hey. You're alright," Jay suddenly swam into his vision.

It took a couple of minutes for Will to get his voice to work. "Hai-ley," he choked out.

"I really hope the next time we hang out, you'll let me bring my gun, Halstead. Also, if we are put in a similar situation, keep your big mouth shut," Hailey entered his field and Will could hear his heart monitor slow down. 

"Can-Can't promise," he croaked, "jus' slips out."

"I'll bet," she rolled her eyes but brought a straw to his lips. Will took small sips before turning his attention to Jay.

"'M sorry," he whispered. 

"What, did you call that man to come in with a gun and take a whole diner hostage," Jay rose an eyebrow at him. 

"Antagonized...didn't tell Hails 'til too late."

"Your mouth's always gotten you into trouble, Bro. I honestly expected nothing less when we got the details from Hailey while you were antagonizing him about being surrounded by the cops...don't look at me like that. Hailey kept the channel open. I'll be getting you into a hostage negotiation course at the academy in case, God forbid, something like this happens again. You're honestly really lucky he didn't shoot you in the first time you opened your mouth." Will could see the concern in Jay's eyes and he felt bad about it. He never wanted to worry Jay. He was the big brother after all. He was supposed to look out for Jay, not the other way around.

"I jus' di'nt want him," he took a breath, "di'nt want him hurt s'meone else. 'Spose fix shit, tried to fix it."

Jay placed a hand on his shoulder. "I know, Brother. You did good. Just...don't do it again. Now, get some rest. I'll see when I can spring you from this joint."

**Author's Note:**

> Also, don't kill me....I promise not all of them will end without the comfort part of the tags.


End file.
